US2024164202A1PendingUtilityA1

Organometallic complex, and organic light-emitting device, display apparatus, image pickup apparatus, electronic apparatus, lighting apparatus, and moving object containing the organometallic complex

Assignee: CANON KKPriority: Jul 6, 2021Filed: Dec 29, 2023Published: May 16, 2024
Est. expiryJul 6, 2041(~14.9 yrs left)· nominal 20-yr term from priority
H10K 2101/10H10K 50/11H10K 85/342C07F 15/0033C09K 11/06C09K 2211/1033C09K 2211/185H10K 50/81H10K 50/82H10K 59/1213H10K 59/123H10K 59/65H10K 59/90C07D 405/04
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Claims

Abstract

The present disclosure provides an organometallic complex represented by the following general formula (1). In general formula (1), M is a metal atom selected from Ir, Pt, Os, Rh, Pd, and Ru. R 1 to R 8 are each independently selected from a hydrogen atom and a substituent. At least one of R 1 to R 8 is the substituent, or at least any of R 9 and R 10 is the alkyl group having two or less carbon atoms.

Claims

exact text as granted — not AI-modified
1 . An organometallic complex represented by the following general formula (1):    general formula (1)   
       where in general formula (1), M is a metal atom selected from Ir, Pt, Os, Rh, Pd, and Ru, R 1  to R 8  are each independently selected from a hydrogen atom and a substituent, the substituent is a halogen atom, a cyano group, a nitro group, a trialkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group having two or less rings, R 9  and R 10  are each independently selected from a hydrogen atom and an alkyl group having two or less carbon atoms, provided that at least one of R 1  to R 8  is the substituent, or at least any of R 9  and R 10  is the alkyl group having two or less carbon atoms. 
     
     
         2 . An organometallic complex represented by the following general formula (1):    general formula (1)   
       where in general formula (1), M is a metal atom selected from Ir, Pt, Os, Rh, Pd, and Ru, R 1 , R 2  , and R 4  to R 8  are each independently selected from a hydrogen atom and a substituent, the substituent is a halogen atom, a cyano group, a nitro group, a trialkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted phenyl group, R 3  is selected from a hydrogen atom, a halogen atom, a cyano group, a nitro group, a trialkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group, and R 9  and R 10  are each independently selected from a hydrogen atom and an alkyl group having two or less carbon atoms, provided that none of R 1  to R 8  are not hydrogen atoms, or at least any of R 9  and R 10  is the alkyl group having two or less carbon atoms. 
     
     
         3 . An organometallic complex represented by the following general formula (1):    general formula (1)   
       where in general formula (1), M is a metal atom selected from Ir, Pt, Os, Rh, Pd, and Ru, R 1  to R 8  are each independently selected from a hydrogen atom and a substituent, the substituent is a halogen atom, a cyano group, a nitro group, a trialkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, R 9  and R 10  are each independently selected from a hydrogen atom and an alkyl group having two or less carbon atoms, provided that at least any of R 9  and R 10  is the alkyl group having two or less carbon atoms. 
     
     
         4 . The organometallic complex according to  claim 1 , wherein R 1  to R 4  are each independently selected from a hydrogen atom and the alkyl group. 
     
     
         5 . The organometallic complex according to  claim 1 , wherein R 5  to R 8  is a hydrogen atom or the alkyl group. 
     
     
         6 . The organometallic complex according to  claim 1 , wherein R 9  is the alkyl group having two or less carbon atoms. 
     
     
         7 . The organometallic complex according to  claim 1 , wherein each of R 9  and R 10  is a hydrogen atom. 
     
     
         8 . The organometallic complex according to  claim 1 , wherein R 3  is a tert-butyl group. 
     
     
         9 . The organometallic complex according to  claim 1 , wherein the metal atom is Ir. 
     
     
         10 . The organometallic complex according to  claim 1 , wherein the organometallic complex is represented by any of the following structural formulae (1) to (5):    
       chemical chemical chemical chemical chemical formula (1) formula (2) formula (3) formula (4) formula (5). 
     
     
         11 . An organic light-emitting device, comprising:
 a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode,   wherein the organic compound layer contains the organometallic complex according to  claim 1 .   
     
     
         12 . An organic light-emitting device, comprising:
 a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode,   wherein the organic compound layer contains the organometallic complex according to  claim 2 .   
     
     
         13 . An organic light-emitting device, comprising:
 a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode,   wherein the organic compound layer contains the organometallic complex according to  claim 3 .   
     
     
         14 . The organic light-emitting device according to  claim 11 , wherein the organic compound layer is a light-emitting layer, the light-emitting layer further contains a first organic compound, and
 the first organic compound is a compound having a higher lowest excited triplet energy than the organometallic complex.   
     
     
         15 . The organic light-emitting device according to  claim 14 , wherein the light-emitting layer further contains a second organic compound, and a lowest excited triplet energy of the second organic compound is equal to or higher than the lowest excited triplet energy of the organometallic complex and equal to or lower than the lowest excited triplet energy of the first organic compound. 
     
     
         16 . The organic light-emitting device according to  claim 14 , wherein the organic compound layer further includes a first charge transport layer disposed between the first electrode and the light-emitting layer, and a second charge transport layer disposed between the second electrode and the light-emitting layer,
 the first electrode is in contact with the first charge transport layer, and the second electrode is in contact with the second charge transport layer.   
     
     
         17 . The organic light-emitting device according to  claim 16 , wherein the lowest excited triplet energy of the first charge transport layer is higher than the lowest excited triplet energy of the first organic compound, and the lowest excited triplet energy of the second charge transport layer is higher than the lowest excited triplet energy of the first organic compound. 
     
     
         18 . A display apparatus, comprising:
 multiple pixels, at least one of the multiple pixels including the organic light-emitting device according to  claim 11 , and a transistor coupled to the organic light-emitting device.   
     
     
         19 . An image pickup apparatus, comprising an optical unit including multiple lenses, an image pickup device configured to receive light passing through the optical unit, and a display unit configured to display an image captured by the image pickup device,
 wherein the display unit includes the organic light-emitting device according to  claim 11 .   
     
     
         20 . An electronic apparatus, comprising a display unit including the organic light-emitting device according to  claim 11 , a housing provided with the display unit, and a communication unit being disposed in the housing and communicating with an outside. 
     
     
         21 . A lighting apparatus, comprising a light source including the organic light-emitting device according to  claim 11 , and a light diffusion unit or an optical film configured to transmit light emitted from the light source. 
     
     
         22 . A moving object, comprising a lighting unit including the organic light-emitting device according to  claim 11 , and a body provided with the lighting unit.

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